Sailors from ships moored in the Pool of London flocked to the Highway. Most were single men with plenty of cash to spare after long voyages. They were looking for drink and women, and the taverns and brothels along its length provided for their every need.

Shanties

Songs and shanties were written in celebration of the Highway. This bawdy example is actually called 'The Ratcliffe Highway'.

During the 17th century the area around the Highway attracted prostitutes of several nationalities. There was an influx of Flemish women who had a reputation for their sexual expertise, and Venetian courtesans. The Venetians were too expensive for most sailors and were patronized by aristocrats and members of the royal court.

One of the most notorious women in the 1650s was Damaris Page. Samuel Pepys described her as 'the great bawd of the seamen'. She was born in Stepney around 1620, became a teenage prostitute and married a man called William Baker in 1640.

During the following 15 years she moved from being a prostitute to running brothels. She owned two. The one on the Ratcliffe Highway catered for ordinary seamen. The second, in Rosemary Lane, was for naval officers and those who could afford more expensive prostitutes.

In 1653 Damaris married a second husband and two years later was brought before Clerkenwell Magistrates. The first charge of bigamy was dismissed on the grounds that her first marriage had not been sanctified. But the second charge, of killing one Eleanor Pooley while attempting to carry out an abortion with a fork, was far more serious.

She was convicted of manslaughter and sentenced to hang. Luckily, she was pregnant at the time and was instead given three years in Newgate. On her release she resumed her career as a madam and died a rich woman in her house on Ratcliffe Highway in 1669.